Acetic Acid → tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamate

HRID 80985Notes

Reaction equation

HRID 80985 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[NH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].C(O)(=O)C>ClC(Cl)C>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67134877tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (3.3 g, 15.4 mmol, 1.1 eq.) was added at room temperature to a solution of 4-chlorobenzaldehyde (2 g, 14 mmol), tert-butyl 2-aminoethylcarbamate (4.5 mL, 28.5 mmol, 1.2 eq.) and acetic acid (2.5 mL) in dichloroethane (20 mL). The reaction mixture was allowed to stir overnight before being quenched with 0.5M HCl (30 mL). The mixture was then extracted with dichloromethane one time and then brine was added. The precipitate was filtered and dried to give tert-butyl 2-(4-chlorobenzylamino)ethylcarbamate (3.58 g, 90%), MS (ESI) m/e (M+H+) 285.

Workup

  1. custombefore being quenched with 0.5M HCl (30 mL)
  2. extractionThe mixture was then extracted with dichloromethane one time
  3. additionbrine was added
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-394bbebeab5740ebb021c6385dbd8b9e
Source dataset
uspto-grants-2014_09
Patent number
US08846683B2

Reaction notes

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